What to know about Judge Raymond Dearie, the Mar-a-Lago search special master

By Jasper Ruppert

Published September 16, 2022 at 5:00 AM EDT

A courtroom sketch of Judge Raymond Dearie in New York in January 2013.

Judge Aileen Cannon has appointed Judge Raymond Dearie as the special master to review documents seized during a court-approved search of former President Donald Trump's Florida home in August.

Dearie, 78, a former chief judge of the federal court in the Eastern District of New York, was one of the special master candidates suggested by Trump whom the Justice Department did not object to.

Cannon directed Dearie to issue interim reports and recommendations "as appropriate" during the review and set a Nov. 30 deadline to complete his work. The Justice Department has said it will appeal the order for a special master.

Here's what you need to know about the special master's background.

Dearie was appointed by Reagan

Republican President Ronald Reagan appointed Dearie, then 41, to serve as a federal judge in New York in 1986, and he assumed senior status in 2011. Justice Department lawyers have said that Dearie has "substantial judicial experience" and is thus qualified for the special master job.

Dearie got his law degree from St. John's University School of Law in 1969 and then eventually served as an attorney for the Eastern District of New York before Reagan tapped him to serve as a judge. He went on to serve as chief judge from 2007 to 2011.

People interviewed by NPR who know Dearie describe him as "fair"

Andrew Weissmann, a federal prosecutor, a former senior member of special counsel Robert Mueller's team and a special master himself, described Dearie as "compassionate" and "fair" and the "platonic ideal of what you want in a judge."

"If you asked both prosecutors and lawyers, they would say the same thing, that he is just so fair," Weissmann said. "It's unusual to have a judge where both sides just have enormous praise for somebody."

When Weissmann was starting out as a federal prosecutor in Brooklyn, the judge was late for a court appearance. "A few days later, I got in the mail a handwritten apology from him," Weissmann recalled. The defense lawyer got the same letter from the judge. "It was just remarkable because judges have a lot of power — they don't need to do that," Weissmann said.

And in a statement to NPR, Daniel R. Alonso, partner at Buckley LLP and a former assistant U.S. attorney in the Eastern District of New York, called Dearie an "old-school gentleman and unfailingly polite."

"Judge Dearie is a judge who, though unfailingly fair, would never tolerate the kinds of arguments that Trump's lawyers tend to put forward," Alonso said.

Dearie served a seven-year term on the U.S. Foreign Intelligence Surveillance Court

In this role, Dearie was one of the judges who approved an FBI and Justice Department request to surveil Carter Page, then a foreign policy adviser to the Trump campaign.

This was part of the inquiry to find out whether Russia had meddled with the 2016 presidential election. There were several errors by the FBI in this process, according to the Justice Department's Office of the Inspector General, and of the four surveillance warrants granted by the FISA court, two were declared invalid, including one approved by Dearie.

Mob figures and al-Qaida are featured in some of his most prominent cases

During his active time as judge at the U.S. District Court in Brooklyn, N.Y., Dearie sentenced Abid Naseer to 40 years in prison. The Pakistani was a member of al-Qaida and plotted, but didn't carry out, attacks on a shopping center in Manchester, England; the New York City subway system; and a Danish newspaper. Naseer had faced a possible life sentence.

Naseer, who represented himself in court, tried to appeal to the judge as someone who was not a threat to society. "Dear judge, it is true I have spent most of my life in search of studies and not extremism and fundamentalism,'' he said. ''I'm not, nor have I been, a career criminal.'' Dearie replied: ''I know you're not. You're a terrorist.''

Dearie also handled cases involving organized crime, including one against the head of a crime family who made attempts to falsify a mental illness to try to avoid standing trial, including appearing in pajamas and a bathrobe in the streets, talking to himself and even urinating in public. He was later sentenced, but not by Dearie.

In recent years, Dearie has become an advocate for sentencing reform

In remarks to the New York Criminal Bar Association in 2016, he called for the criminal justice system to be "rethought and retooled significantly."

"If society relies on the jail cell alone to bring relief to the streets of New York or Chicago, or to fight the heroin epidemic that has invaded our communities, little will change," he said, adding that he wondered "how we as a society would fare if we took a fraction of the money we spend on warehousing people and invested it in programs to reach those vulnerable to the hollow call of the streets."

Dearie admitted that at times, he wanted "to scream out in frustration, sadness and anger" when he was required to impose a mandatory sentence.

He continued:

We too often ignore the issues, the causes, the needs, sit back as a society, wait for them to commit crimes, prosecute them with great gusto, root for a stiff sentence and then pat ourselves on the back for a job well done, too often filling the prisons with scores of nonviolent offenders, often destroying the salvageable with cruelly lengthy sentences and risking the well-being of innocent family members.

After 36 years on the bench, Dearie moved to inactive status

In August, Dearie decided he wanted to move to an inactive status as a judge, a step just short of formal retirement. But it's unclear yet when that shift will eventually happen, one of his staff members told NPR. As an inactive judge, Dearie could return to the bench, if needed.

"I'm going to miss it," he told New York Law Journal.